“Bounded on the north by crabs, on the east by fresh fish, and on the south by mosquitoes” is how one visitor described an island he loved just off Maryland’s Eastern Shore, and with minor shifts of the compass, the description holds good for most of the region. By fall many of the mosquitoes have departed, but in almost any town along the water, you’ll see long, narrow crab boats piled high with the bushel baskets the watermen use to bring home their catch. The boats have no-nonsense names painted across their transoms, names like Hattie Walker and Hard Times . St. Michaels, located on the middle of a peninsula halfway down the bay, makes a good central base for exploring the area, especially because of the presence here of the Chesapeake Bay Maritime Museum.

Until a bridge went up in 1952, connecting Annapolis with the counties across the bay, the Eastern Shore was one of the most isolated sections of the East Coast, inhabited mostly by farmers and fishermen. On Rand McNally’s map of Maryland, the road to St. Michaels is marked with the broken yellow line that signifies “Scenic Route.” In October fields of pumpkins and dried cornstalks line the way. The fields run right down to the bay and to the banks of the rivers that feed into it: the Miles, the Choptank, the Tred Avon, the Nanticoke.

As you enter town, Route 33 becomes Talbot Street, bordered for a few blocks with stores selling T-shirts and gourmet relishes. St. Michaels is a village of narrow streets, small lots, and modest houses with no yards to speak of. By way of compensation, everybody has a porch, and many people have two, one at street level, another upstairs. Fitted out with couches and rockers and potted plants, the porches clearly serve as living rooms; it gets warm here in July and August. St. Michaels has flourished in recent summers, and most of the houses look well cared for. But every now and then you come across one with a sagging roof and peeling exterior—a reminder that this has always been a hardworking town.

Situated close to forests of oak and pine, St. Michaels grew up in the Federal era as a shipbuilding center. Its best-known citizen is the great abolitionist Frederick Douglass, who lived and labored here against his will in the 1830s. By that time Baltimore’s shipyards had eclipsed those of St. Michaels, and in his autobiography, My Bondage and My Freedom , Douglass describes the town as wearing “a dull, slovenly, enterprise-forsaken aspect.” Most of the houses “had never enjoyed the artificial adornment of paint, and time and storms had worn off the bright color of the wood, leaving them almost as black as buildings charred by a conflagration.” His memories of the local fishermen, who constantly drank liquor, “the then supposed best antidote for cold,” are even less fond. A small park on Talbot Street is dedicated to Douglass, and local bookstores sell copies of his extraordinary memoir.

Just off the park Mill Street leads to the water and the Chesapeake Bay Maritime Museum. The day I arrived, I was drawn there by what sounded like wild applause. The weather had just cleared after a dramatic early-morning thunderstorm, and at first I thought people must be clapping in gratitude for this improvement in the day. But it turned out that fifty kids under a striped tent were hammering nails into the model boats they were building as part of the museum’s annual Mid-Atlantic Small Craft Festival.

Founded in 1965, the museum is engaged in preserving the maritime culture and history of the Chesapeake Bay region. Exhibits are spread out in an attractive assortment of small-scale buildings transplanted from around the region, including a bandstand from a steamer landing at Tolchester Beach and a lighthouse that once marked Hooper Strait, thirty-four miles down the bay. Jim Thomas, a ruddy, white-haired retired ship’s officer who is now a museum volunteer, took me around, recounting with some pride St. Michaels’s role in the early history of the nation. Privateers built here were responsible for capturing scores of British ships, he told me. “It got so bad that in 1813 King George sent a naval squadron with orders to ‘burn Norfolk, burn Washington, burn Baltimore. And while you’re at it, clean out that nest of pirates in St. Michaels too.’” A small force did attack the town in August of 1813 and was repulsed by an even smaller one, all but three members of the local militia having scattered after the first volley. One building in town took a shot through the roof and is known as Cannonball House to this day. Both sides claimed victory, and, sadly, the town’s proudest memory—that on the night of the attack residents drew British fire away from St. Michaels by hanging lanterns in trees outside town—seems never to have happened.

After this dose of what Jim Thomas apologetically called “serious history” he led the way to the small boats that are closer to his heart and mine, boats that have provided St. Michaels with its livelihood since the British went away. He showed me a sixteen-foot skiff supporting a nine-foot gun—the kind used in the nineteenth century to bring down entire flocks of geese or ducks with a single shot—and several sailing canoes made of logs joined side by side with iron drifts. Until recently, Thomas told me, “if you had an eighteen-year-old son and he brought home a new bride, you’d take him up in the woods, cut down five or eight logs, borrow a neighbor’s ox team, haul the logs down to the water, and build a boat. As soon as it was done, you’d say, ‘So long, you’re on your own.’” Today fewer than twenty log canoes remain sailing on the bay. Their races, held several times during the summer, are so hotly contested that the owners pile on as many extra sails as they can find room for. Then, to balance the overcanvassed craft, crew members hike out on long boards for extra leverage. Capsizes are frequent, not dangerous, and comical to watch.

In addition to its canoes, the museum has the Chesapeake’s last remaining log bugeye rigged for sail, and two skipjacks, the larger, beamier craft designed in the 1890s expressly to catch oysters. The bay’s skipjack fleet is in danger of disappearing as disease gradually kills off the oyster population. If you drive to Dogwood Harbor on Tilghman Island, just twelve miles past St. Michaels, you can see as many as fifteen of them rafted together. They’re the last sail-powered commercial fishing boats in the country.

Thomas has sailed on skipjacks, fished from crab boats, and worked as a marine surveyor, and when he took me to the Hooper Strait lighthouse, moved in 1966 to the museum’s grounds, it turned out he had been at the wheel of the salvage boat that carried it there. Built in 1879, the low, hexagonal building had marked a channel. Now visitors can climb its spiral staircase for a view of St. Michaels Harbor and a look at the lighthouse keeper’s life of a century ago. In addition to keeping the oil lamp burning, in fog or snowstorms the keeper cranked up by hand a massive steel cable that would then slowly unwind, sounding a bell three times every thirty seconds. The job had to be tended to every two hours day and night. “Worse than a baby,” said a visitor behind me.

Saying good-bye to Jim Thomas, I remembered what Hulbert Footner had written about the area and the sociability of its residents in his excellent local history Rivers of the Eastern Shore . “The waters are full of food; until recent years there was game for everybody also; the garden will produce two or three crops in a season. . . . Hardship may be good for the character; ease develops the personality.”

From St. Michaels it’s a ten-minute drive to Bellevue, where you can put your car on a small ferry (in business off and on since 1683) and cross over to Oxford, a tranquil colonial-era town with broad streets and tall trees, a place remarkably undisturbed by tourism. Many of the old houses have disappeared, but the Robert Morris Inn, built in 1710, gives a sense of how they must have looked. The one-room customhouse, a replica of one from the 1790s, reminds visitors that Oxford once served as the trading center for the Eastern Shore; its tiny size suggests how little paperwork this entailed.

Some visitors stay overnight in Oxford, but the quiet made me miss the energy of St. Michaels, and I headed back to dine on crabs at one of the restaurants overlooking the water. An oversized, salmon-colored moon lifted out of the bay, and as the sky grew dark, a cluster of sailboats moored in the harbor turned on the white lights they’re required to show at the tops of their masts. From the shore the lights looked like low-flying stars, or like lanterns hung to fool the British.